We experimentally demonstrate the record long-haul orbital angular momentum (OAM) mode-division multiplexed (MDM) transmission over 300-km assisted by a ring-core fiber (RCF) recirculating loop. The recirculation loop consisting of 50-km RCF is controlled mainly by two acousto-optic switches with opposite states, and the signals are cyclically transmitted in the single-span 50-km RCF to achieve long-haul transmission. The RCF features largely separated OAM mode groups, where the effective refractive index difference between adjacent high-order OAM mode groups is larger than 1.0 × 10-3. Due to the low-crosstalk feature of RCF incorporated into fiber optic links, multiple-input multiple-output (MIMO) equalization technology is not used in the OAM MDM system. We transmit 20-Gbit/s quadrature phase-shift keying signals over two high-order OAM modes, and the transmission performance is characterized. The measured average optical signal-to-noise ratio penalties at a bit-error rate of 1.5 × 10-2 are about 2 dB between single OAM mode transmission and OAM modes multiplexing transmission. The obtained experimental results indicate favorable OAM-based MDM transmission performance in a 300-km recirculating loop link.